4883-60-7

Basic information

• Product Name: 3,5,5-TRIMETHYLCYCLOHEXANE-1,2-DIONE
• Synonyms: 2-HYDROXY-3,5,5-TRIMETHYL-2-CYCLOHEXENONE;2-Cyclohexen-1-one, 2-hydroxy-3,5,5-trimethyl-;2-HYDROXY-3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-ONE;2-Hydroxy-3，5，5-trimethylcyclohex-2-en-1-one;2-Hydroxyisophorone;Fema no. 3459;3,5,5-Trimethyl-1,2-cyclohexanedione 2-Hydroxyisophorone;2-Hydroxy-3,5,5-Trimethyl-2-Cyclohexen-1-One(FEMA:3459)
• CAS NO: 4883-60-7
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.21
• EINECS: 1312995-182-4
• Mol File: 4883-60-7.mol

Chemical Properties

• Melting Point: 89-90°C
• Boiling Point: 100°C/13mmHg(lit.)
• Flash Point: 108.5 °C
• Appearance: colourless to pale yellow solid
• Density: 1.044 g/cm³
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: 1.444
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 9.15±0.40(Predicted)
• BRN: 1932034
• CAS DataBase Reference: 3,5,5-TRIMETHYLCYCLOHEXANE-1,2-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,5-TRIMETHYLCYCLOHEXANE-1,2-DIONE(4883-60-7)
• EPA Substance Registry System: 3,5,5-TRIMETHYLCYCLOHEXANE-1,2-DIONE(4883-60-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4883-60-7(Hazardous Substances Data)

Usage

Occurrence

Reported found in burley tobacco.

Synthesis Reference(s)

Journal of the American Chemical Society, 103, p. 686, 1981 DOI: 10.1021/ja00393a040

InChI:InChI=1/C9H14O2/c1-6-4-9(2,3)5-7(10)8(6)11/h6H,4-5H2,1-3H3/t6-/m0/s1

Upstream product

• 10276-21-8 isophorone oxide 
• 873-94-9 dihydroisophorone 
• 17304-83-5 2-Ethylmercapto-3,5,5-trimethyl-cyclohexen-⁽²⁾-on 
• 319916-44-4 3,5,5-trimethyl-2-(6-methyl-pyridin-2-yloxy)-cyclohex-2-enone 

Downstream Products

• 97041-23-1 3,6-dichloro-2-hydroxy-4,4,6-trimethyl-2-cyclohexenone 
• 97041-25-3 3-Chloro-2-hydroxy-2-methoxy-3,5,5-trimethyl-cyclohexanone 
• 97041-28-6 3-chloro-2-hydroxy-4,4,6-trimethylcyclohexadienone 
• 97041-22-0 6-chloro-2-hydroxyisophorone 
• 28750-52-9 2-hydroxy-4,4,6-trimethylcyclohexa-2,5-diene-1-one 
• 97041-24-2 3-Chloro-3,5,5-trimethyl-cyclohexane-1,2-dione 
• 97041-27-5 (3S,6S)-3,6-Dichloro-3,5,5-trimethyl-cyclohexane-1,2-dione 
• 4883-61-8 (+/-)-3,3,6-Tribrom-4,4,6-trimethyl-cyclohexan-1,2-dion 

Relevant articles and documents

Practical preparation of diosphenols by ring opening of α,β-epoxyketones catalyzed by silica gel supported acids

The mixed acid (H2SO4-HOAc) catalyzed ring opening of α,β-epoxyketone was the most used method for the preparation of diosphenols, but it seriously suffered from poor yields and tedious workup operations. By using silica gel supported mixed acid (H2SO 4-HOAc), a variety of α,β-epoxyketones were converted into the corresponding diosphenols in unprecedented high yields within a few minutes. Georg Thieme Verlag Stuttgart.

Opening of epoxide rings catalyzed by niobium pentachloride

The behavior of several epoxides when treated with NbCl5 was studied. In general, the studied epoxides reacted rapidly with NbCl5, giving, in most cases, more than one product (chlorohydrins, products containing solvent residues, as well as rearrangement products). A detailed study was performed to verify the effects of the temperature (rt, 0°C, or -78°C) and of the NbCl5 molar concentration on the composition of the products, yield, and time required for the reactions. Copyright Taylor & Francis Group, LLC.

Niobium pentachloride catalysed ring opening of epoxides

Epoxide ring opening is a frequently required transformation in Organic Synthesis. In this paper we describe the application of NbCl5 for this purpose using three different substrates. Chlorohydrins, 1,2-diols, products containing solvent resid

Conversion of α,β-epoxyketones to diosphenols using 6-methyl-2-pyridone anion as an hydroxide equivalent

Treatment of α,β-epoxyketones with 6-methyl-2-pyridone anion gives diosphenol (6-methyl-2-pyridyl) ethers that can be cleaved to diosphenols under mild basic conditions. (C) 2000 Elsevier Science Ltd.

A New Synthesis of 3-Alkyl-1,2-cyclohexanediones from 2-Alkylcyclohexanones Using Iodine/Copper(II) Acetate

The reactions of 2-alkyl-, 2,5-dimethyl-, and 3,3,5-trimethylcyclohexanone with iodine/copper(II) acetate in boiling aqueous acetic acid gave the respective 3-alkyl-, 3,6-dimethyl-, and 3,5,5-trimethyl-1,2-cyclohexanediones in 40-70percent yields.This new

IMPROVED SYNTHESIS OF 2-HYDROXY-4,4,6-TRIMETHYL-2,5-CYCLOHEXADIENONE, USEFUL AS A FLAVORING ADDITIVE

The title dienone 1, useful for modification, improvement or increasing organoleptic properties of tobacco, sucrose syrups, flavored beverages, was prepared in 40-55percent overall yield from isophorone, by chlorination of 2-hydroxy-isophorone (2), rearrangement into 6-chloro-2-hydroxyisophorone (5) and dehydrochlorination.An excellent yield of 3-chloro-2-hydroxy-4,4,6-trimethyl-2,5-cyclohexenone (12) was obtained by chlorination of 5 followed by dehydrohalogenation.